What happens when momentum hits and your biggest challenge becomes keeping up?

In this episode of TinySeed Tales, Rob Walling catches up with Harris Kenny, founder of OutboundSync. Revenue is growing, the team is moving fast, and enterprise leads are coming in. But with success comes complexity: support load, pricing strategy, and product demands are all increasing. Harris is hiring again, learning to say no, and figuring out how to keep the momentum without losing focus.

• (1:40) – Closing his biggest deal ever and what it unlocked
• (4:26) – Learning how to do enterprise sales
• (6:20) – How SOC 2 made the product stronger
• (12:18) – New hires are paying off
• (18:23) – Building the Salesforce integration
• (22:13) – Getting pull from the market, not pushing
• (24:10) – Taking customers from unicorns

• TinySeed SaaS Accelerator - Applications close on September 9th
• Coaching Call Bonus
• Invest in TinySeed
• YNAB (You Need A Budget)
• Dynamite Jobs
• OutboundSync
• Harris Kenny | LinkedIn

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

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Is GPT-5 a real risk for SaaS founders, or just the beginning of a new chapter?

In this Hot Take Tuesday, Rob Walling, Einar Vollset, and Tracy Osborn dig into GPT-5’s mixed reviews, signs of stress in the A.I. bubble, and how Windsurf’s $2.4B exit left early employees with nothing. They also unpack why returning a VC fund is such a rare (and big) deal.

This episode is brought to you by Gearheart.io, which specializes in helping early-stage founders validate ideas, prototype SaaS products, and build AI-powered MVPs with real user testing, so your code won’t crumble when your first customers show up.

Founded by entrepreneurs who’ve launched and exited their own startups, Gearheart has helped launch over 70 B2B SaaS products, including SmartSuite (which raised $38 million). They get where you’re at.

Book your free strategy session at gearheart.io and mention Startups for the Rest of Us to get 20% off discovery, validation, or prototyping services.

• (3:12) – TinySeed returns Fund One
• (9:40) – GPT-5: Upgrade or letdown?
• (19:19) – Are we in an AI bubble?
• (24:09) – The Windsurf debacle: $2.4B exit, $0 for early employees
• (31:06) – The bigger problem: Are startups forgetting to share the upside?
• (40:05) – Lifestyle vs. Ambitious Bootstrapping

• TinySeed Fall 2025 Applications Live Q&A - Join us Wednesday September 3rd
• TinySeed SaaS Accelerator - Applications are Open!
• Invest in TinySeed
• MicroConf
• SaaS Institute
• Discretion Capital
• Einar Vollset | LinkedIn
• Einar Vollset (@einarvollset) | X
• Tracy Osborn
• Tracy Osborn | LinkedIn
• Tracy Osborn (@tracymakes) | X

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

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In this episode of TinySeed Tales, Rob Walling reconnects with Harris Kenny, founder of OutboundSync, to explore the rapid evolution of his SaaS business just months after transitioning from agency work.

Harris shares how niching down to outbound-focused agencies unlocked sales momentum. He talks about hiring, his Salesforce breakthrough, SOC 2 prep, and why finally spending his TinySeed funding changed everything.

• (2:27) – Launching a lower-priced version and building expansion revenue
• (6:40) – How lead-gen shops are outpacing legacy rev ops
• (12:01) – Hiring full-time: Dev speed, onboarding load, and customer success firepower
• (18:15) – A surprise Salesforce breakthrough and what it means for product strategy
• (24:42) – SOC 2 prep, pricing confidence, and finally spending the TinySeed check

• Join the TinySeed Mailing List
• Apply for TinySeed - Applications reopen September 1, 2025
• OutboundSync
• Harris Kenny | LinkedIn
• Coaching Call Bonus
• Dynamite Jobs
• Vanta

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

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How can you scale yourself as a founder?

In this episode, Rob Walling is joined by Yaniv Bernstein (co-founder and CTO of Violet, former COO, VP of Engineering, and Google leader) to unpack how a founder’s role must change as the company grows. From writing the code yourself to leading managers of managers, they dig into the tough transitions every founder faces, and what happens if you don’t adapt.

• (3:27) – How the founder/CEO role changes as your SaaS scales
• (8:44) – The turning point where systems and processes matter
• (14:49 – When to hand off marketing, sales, or product as a founder
• (19:44) – Why setting context is your #1 job as a founder-CEO
• (28:19) – Why hiring right (and firing fast) makes or breaks scaling

• SaaS Institute
• MicroConf | The community for SaaS founders
• MicroConf YouTube Channel
• People Engineering
• The SaaS Playbook
• Yaniv Bernstein | LinkedIn
• Yaniv Bernstein (@ybernsteindig) | X
• The Startup Podcast

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

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Welcome to Season 5 of TinySeed Tales, the documentary-style series where we follow one SaaS founder’s journey over 12 months to hear about the wins, the missteps, and everything in between.

In this season premiere, Rob Walling introduces Harris Kenny of OutboundSync. After running a successful agency, Harris makes the leap to go all-in on SaaS. It’s a high-stakes transition that many agency owners are never able to make.

Topics we cover:

• (2:25) – From agency owner to TinySeed-backed SaaS
• (6:38) – Walking away from consistent agency revenue to go all-in on SaaS
• (13:51) – Going all-in vs. splitting focus
• (16:13) – Why most agencies fail at SaaS
• (28:15) – What’s working, what’s not, and what’s next

• Join the TinySeed Mailing List - Applications reopen in September 2025
• Apply for TinySeed
• Coaching Call Bonus
• MicroConf Connect
• OutboundSync
• The SaaS Playbook
• Harris Kenny | LinkedIn

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

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What are the real risks of AI-generated code and “vibe coding”?

In this episode, Rob Walling is joined once again by fan-favorite Derrick Reimer to answer a fresh batch of listener questions. They dig into solo vs. co-founder trade-offs, managing scope creep, and how integrations can shape early traction.

Want to get your questions answered? Drop them here.

• (2:33) – Do you need a co-founder to succeed in SaaS?
• (5:18) – The Risks of AI-Generated Code and “Vibe Coding”
• (13:50) – How to manage scope creep as a solo founder
• (23:32) – Finding and retaining great contractors
• (39:43) – How to build a startup culture with a bias for action

• MicroConf Europe | Istanbul, Sep 28-30, 2025
• TinySeed Tales Podcast
• MicroConf Connect
• TinySeed Fund
• SavvyCal
• Derrick Reimer | LinkedIn
• Derrick Reimer (@derrickreimer) | X

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

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How do you know it’s time to move on from a product that’s growing?

In this episode, Rob Walling chats with Braden Dennis, co-founder of Fiscal.ai (formerly FinChat), about a rare founder journey: bootstrapping, catching lightning in a bottle, and choosing to go big with venture capital. They dive into the emotional and strategic weight of shutting down a $1.5M ARR product, what shifts when you scale past 40 people, and why Braden prioritized long-term vision over short-term revenue.

• (2:30) – From FinChat to Fiscal.ai: rebranding and repositioning
• (6:50) – Why they raised a $10M Series A
• (13:09) – From bootstrapped to venture-backed: what changes?
• (19:56) – Becoming a real CEO at 25 employees
• (26:44) – Why they shut down a $1.5M product
• (30:30) – Lessons from having four co-founders
• (33:13) – The benefits of joining TinySeed

• MicroConf Connect
• The Great CEO Within
• TinySeed: SaaS Institute
• Fiscal.ai (formerly FinChat)
• Braden Dennis (@BradoCapital) | X
• Braden Dennis | LinkedIn

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

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How do you really know when you’ve hit product-market fit?

In this episode, Rob Walling welcomes back Kevin Wagstaff, co-founder of Spectora, to answer listener questions about early traction in Facebook groups, finding product-market fit, handling criticism, and what it really took to bootstrap to a $90M exit.

Want to get your questions answered? Drop them here.

(3:15) – Early traction using Facebook groups (7:17) – The tradeoff between growth and work-life balance (12:26) – Participating inside Facebook groups run by rivals (14:39) – Ranking for niche SEO terms (19:06) – Funding the early days through consulting (25:14) – Surviving churn in a seasonal, high-turnover market

• SaaS Institute
• Mark Cuban Blog Post
• Kevin Wagstaff | LinkedIn
• Kevin Wagstaff (@KevinWagstaff3) | X
• Spectora

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify